Conformational studies on 2',3'-unsaturated pentopyranosyl nucleosides by 1H NMR spectroscopy. Impact of π → σ* interactions on the axial preference of the purine versus pyrimidine nucleobase

Journal of the American Chemical Society

Volumn 119, Issue 41, 1997, Pages 9782-9792

  Polak, Matjaž ^a   Doboszewski, Bogdan ^b   Herdewijn, Piet ^b   Plavec, Janez ^a  

^a NATIONAL INSTITUTE OF CHEMISTRY   (Slovenia)

^b REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

NUCLEOSIDE; PURINE NUCLEOSIDE; PYRIMIDINE NUCLEOSIDE;

ARTICLE; CALCULATION; CONFORMATION; CRYSTAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

EID: 0030726062     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja963683k     Document Type: Article

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35. 5 [C4′-C5′-O6′-C1′]
36. 15a by ID difference NOE measurements. Nucleosides 1-5 exhibit H1′ ↔ H5″ and H8/6 ↔ H5′ NOE interactions which unequivocally proves their β-configuration. All α-analogues 6-10 exhibit NOE contacts between H1′ ↔ H4′, H1′ ↔ H5′, and H8/6 ↔ H5″, which proves that H1′, H4′, and H5′ protons are on the β face of the sugar moiety in 6-10 and the α-configuration at the anomeric center. In addition, the NOE interactions between H3′ and H6 in pyrimidine and between H3′ and H8 in purine nucleosides were observed which show that the base adopts Predominantly anti conformation in 1-10.
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40. 2-isobutyrylguanine.